You could say that Bill Gurley is pretty good at what he does. The legendary venture capitalist and general partner at Benchmark has a track record of investing and serving on the boards of now-iconic companies like Uber, Zillow, OpenTable, and Nextdoor.
Bill loves what he does, and like most successful people, is endlessly curious and driven to get better. To that end, he spent a decade researching what separates people who thrive in their careers from those who end up with regret, and wrote about it in his new book, Runnin’ Down a Dream. The book identifies six principles for building a career you’ll actually love, and he joined me on How Success Happens to share those insights, plus a whole lot more. I’ve broken down his best advice to help you steer your career where you want it to go in three, two, one!
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Three Key Insights
The Regrets That Haunt You Are the Things You Didn’t Try
Bill hit me with a stat that immediately hits as true and terrifying: Nearly six in ten people say they would do things differently if they could start their careers over. That’s what he says is the trap of career regret. But here’s the thing — Bill says that it’s not our mistakes that weigh on us most. Referencing author Daniel Pink‘s research, Bill explained, “The regrets that hang heaviest on people are the what he calls boldness regrets or regrets of inaction,” Bill explained. “And as we get older, it’s the thing we didn’t do that really weighs on our psyche.” Bill points to Jeff Bezos’s “regret minimization framework”—imagine yourself at 80 and ask if there’s something you’ll wish you had tried. Because it is never too late to do it, he says, pointing to the example of Bert “Tito” Beverage, who created Tito’s Vodka after having careers as a seismologist and mortgage broker.
Takeaway: If you’re holding back on something because you’re afraid of failing, flip the question: Will you regret not trying?
Find Mentors in Two Tiers (And Stop Waiting for Warren Buffett)
When I asked Bill about mentorship, he immediately broke it down into what actually works versus what we fantasize about. “I try and divide it into two places because I think immediately people think they want their mentor to be Warren Buffett and that’s not realistic,” he said. He suggests you create “aspirational mentors” and “pragmatic mentors.” For aspirational ones, study the greats in your field through YouTube videos, podcasts, and their writing—you can learn a lot without ever meeting them. For pragmatic mentors, “find people two tiers down from the greats that no one ever calls. They’ll be flattered if you’re studying them. You might be surprised — 40% of them might say okay.” Different mentors can help with different skills—leadership from one, tactical advice from another. You don’t need one all-knowing Yoda.
Takeaway: Make a list of five people in your field who are successful but accessible, study their work, then reach out with a specific question about what they know that you don’t.
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